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Britney Spears partied all night with Sean ‘Diddy’ Combs before disastrous MTV VMAs 2007 performance

May 25, 2025
in Music, News
Britney Spears partied all night with Sean ‘Diddy’ Combs before disastrous MTV VMAs 2007 performance
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Britney Spears partied all night with Sean “Diddy” Combs before her disastrous performance at the 2007 MTV Music Video Awards.

Resurfaced photos of the “Toxic” songstress show her smiling alongside the Bad Boys Records founder at Jet nightclub in Las Vegas on Sept. 7, 2007.

Later that night, Spears joined Combs, Paris Hilton and 50 Cent at the Hard Rock Hotel & Casino for another party hosted by the “In da Club” rapper.

Britney Spears (L) and P. Diddy (R) attend an evening at PURE Nightclub hosted by P. Diddy on September 7, 2007 in Las Vegas, Nevada.
Britney Spears partied with Sean “Diddy” Combs before her disastrous 2007 MTV Music Video Awards performance. WireImage
Resurfaced photos show the “Toxic” songstress and Bad Boys Records founder at Jet nightclub in Las Vegas on Sept. 7, 2007, before they headed to 50 Cent’s party at the Hard Rock Hotel & Casino. WireImage

The bash continued into the early morning of Sept. 8, 2007, though it’s unclear what time Spears went home.

The photos of the “Womanizer” hitmaker, now 43, partying with Combs, now 55, were unearthed after Casandra “Cassie” Ventura name-dropped Spears during Combs’ ongoing sex-trafficking trial. (The “I’ll Be Missing You” rapper has denied the charges against him.)

The “Me & U” singer, now 38, testified that her relationship with Combs “sort of” began in September 2007 while celebrating her 21st birthday in Las Vegas.

Dallas Austin, Singer Britney Spears, Rapper P. Diddy and Singer Cassie pose for photos at Cassie's 21st Birthday at Jet Nightclub at The Mirage Hotel and Casino on September 08, 2007 in Las Vegas
The night was recently mentioned during Casandra “Cassie” Ventura’s testimony at Combs’ sex-trafficking trial. WireImage
Dallas Austin, Singer Britney Spears, Rapper P. Diddy and Singer Cassie pose for photos at Cassie's 21st Birthday at Jet Nightclub at The Mirage Hotel and Casino on September 08, 2007 in Las Vegas
“Sean was there, and he brought Dallas Austin, Britney Spears. I think those were the two people that stand out to me,” Ventura said in court. WireImage

“Sean was there, and he brought Dallas Austin, Britney Spears. I think those were the two people that stand out to me,” Ventura said in court on May 15.

Spears infamously took the stage at the MTV VMAs on Sept. 9, 2007, to perform her song “Gimme More.”

The performance was expected to be her comeback, but the pop icon faced faced widespread criticism for her lackluster choreography and poor lip-syncing.

Singer Britney Spears, Rapper P. Diddy, 50 Cents, Paris Hilton and Dallas Austin at The Hard Rock on September 8, 2007 in Las Vegas, Nevada.
Spears was pictured with Combs throughout the night. FilmMagic
 Britney Spears performs onstage during the MTV Video Music Awards at The Palms Hotel and Casino on September 9, 2007 in Las Vegas, Nevada.
The pop star infamously performed at the awards show the following night. Getty Images

In her 2023 memoir, “The Woman in Me,” Spears wrote that “nothing was going right” before she performed.

“There was a problem with my costume and with my hair extensions,” she wrote.

“I hadn’t slept the night before. I was dizzy.”

Singer Britney Spears performs onstage during the MTV Video Music Awards at The Palms Hotel and Casino on September 9, 2007 in Las Vegas, Nevada.
Spears recalled the heavily critiqued performance in her 2023 memoir, “The Woman in Me.” Getty Images
Britney Spears performs onstage during the MTV Video Music Awards at The Palms Hotel and Casino on September 9, 2007 in Las Vegas, Nevada.
“I hadn’t slept the night before. I was dizzy,” she wrote in the book. Getty Images

Spears had also bumped into her ex-boyfriend Justin Timberlake — whom she dated from 1999 to 2002 — backstage.

“It had been a while since I’d seen him,” she wrote. “I couldn’t believe I was going to have to go out onstage feeling the way I felt.”

At the time, the “Circus” singer was also facing intense public scrutiny after divorcing Kevin Federline and infamously shaving her head months earlier.

The post Britney Spears partied all night with Sean ‘Diddy’ Combs before disastrous MTV VMAs 2007 performance appeared first on Page Six.

Tags: 50 centBritney Spearscassiecelebrity friendshipsLas VegasMTVparis hiltonpartiesSean "Diddy" Combsvideo music awards
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